First encounters and initial impressions of the 45thPresident of the United States Donald Trump spanning four decades. Liz Smith, Richard Branson, Andy Warhol, Stormy Daniels and other notables recall meeting The Donald.

Liz Smith, gossip columnistKing of hyperbole

…I immediately decided I liked Ivana Trump from afar and was curious. Before long, I met Mrs. Trump, and then I met her tall blond husband. I found them both refreshing, if a bit presumptuous and naïve socially, and I began to note their comings and goings. Little did I dream that their eventual “going” would be something of my “coming” to the fore in newsprint and other media. The Trumps were to have a profound effect on my career.

Donald became bigger and bigger. He was the king of hyperbole and he had just the requisite touch of Elvis vulgarity to endear him to the common man. Whenever he emerged from his chauffeured car on Fifth Avenue to go into his new Trump Tower, or to the recently bought Plaza Hotel, or turned up at the fights or at his new casino in Atlantic City, he would be mobbed by the public. …

Donald would always gather me up under his arm and say to whoever might be near, “She’s the greatest! Isn’t she the greatest?” This was silly and embarrassing and he did it with everybody else as well. Although he was phobic about germs, he was a natural-born toucher and hugger. I enjoyed talking to him, arguing uselessly that he should build low-income housing to help New York’s less well-heeled, or turn the floors of his buildings into rooms for the poor. He laughed at me and I never believed a word he said about how rich he was, how he’d bested the competition and what he intended to do next. It was his singular and special brand of conversation, overlaid with hype. … ( late 1970s)

from Natural Blonde: A Memoir, by Liz Smith ( Hyperion, 2000)

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Edward Koch, New York City mayor (1978-1990)Blowhard

…Let me…use this opportunity to deliver a few parting shots at some of the more prominent New Yorkers…with whom I crossed paths, or swords.

I’ll begin with Donald Trump. What a supreme, egotistical lightweight! This was clear to me from our very first meeting. To be fair, he did build some good-quality buildings, but he was such a blowhard. The best comment I ever heard about Trump came from Alair Townsend, my deputy mayor for economic development, who said she wouldn’t believe Donald Trump if his tongue were notarized. I think the line itself was not original with her, but she found its perfect target.

…Had to meet Donald Trump at the office…Marc Balet had set up this meeting. I keep forgetting that Marc gave up architecture to become an art director, but he still builds models at home, he told me. He’s designing a catalogue for all the stores in the atrium at the Trump Tower and he told Donald Trump that I should do a portrait of the building that would hang over the entrance to the residential part. So they came down to talk about that. Donald Trump is really good-looking. A girl named Evans was with him and another lady. It was so strange, these people are so rich. They talked about buying a building yesterday for $500 million or something. They raved about the Balducci’s lunch, but they just picked at it. I guess because they go around to so many things where there’s food. And they didn’t have drinks, they all just had Tabs. He’s a butch guy. Nothing was settled, but I’m going to do some paintings, anyway, and show them to them. (1981)

from Diaries, by Andy Warhol (Warner Books, 1989)

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Paul Anka, singerGetting into gaming

I met Trump originally through [lawyer] Roy Cohn [whose clients included Trump, as well as a number of Mafia figures].

…Trump, who wanted to be in the casino business and would I meet with him and just give him all my wisdom about casinos, blah-blah-blah-blah.

…into Roy Cohn’s living room…in walks this guy, very sure of himself, making a grand entrance—you expected to see papers flying about the room in his wake—Donald Trump. He was very much a prototype of what he is today, thinner, but with the same kind of confidence—and the same hair. We sat down and I talked to him about the gaming industry, everything that I knew, marketing, etc. So that’s the Cohn-Trump connection. Trump wanted to get into the casino business in the worst way—and wanted to know everything about gambling. …

On an unforgettable wet Monday I researched the half-built Trump Tower, where I had decided that Maxi [a character in her I’ll Take Manhattan] would have an apartment. Donald Trump, who was then merely a bombastic builder named Donald Trump, not a household word, God help us—not yet even “The Donald”—took me all over the structure, proudly showing me the future apartments that were merely beams and holes. Finally he took me up to his own top-floor triplex and insisted that we tour his roof garden, where full-sized trees had already been planted.

“No, I don’t want to,” I protested, “it’s too wet out there. Look, the clouds are covering the treetops. I’ll ruin my hair!” This dread possibility, I thought, would surely bring him to his senses.

“Come on,” he said, grabbing me by the arm, or was it the scruff of my neck? I felt as if I were in the grasp of King Kong, but see his trees I did, and ruin my hair it did, but later on, when Maxi needed money, I wrote a scene in which she sold her apartment back to Donald. I sent the scene to him for vetting, to make sure it could legally happen that way, and he approved. (early 1980s)

from Sex and Shopping: The Confessions of a Nice Jewish Girl, by Judith Krantz (St. Martin’s Press, 2000)

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Susan Mulcahy, gossip columnistEasy access, selective memory

…No matter how well wired a gossip columnist is, there are those who will try to snip those wires—cutting away potential scoops, by denying stories.

Of all the wire cutters I’ve encountered, Donald Trump carries the sharpest instruments.

Trump, the wealthy and influential real estate developer, wasn’t as public a figure as he is now when I first encountered him. On some level, sorry to say, I’ve helped contribute to his profile by writing about him frequently, but he is so outrageous as to be irresistible gossip column copy.

Trump is not blind to the fact that he is appealing to the media, and he doesn’t try to avoid phone calls from reporters. I’ve always appreciated the easy access—not that is has ever made getting the right angle on a Trump story any easier.

“I don’t know anything about it” is Trump’s favorite phrase. He’s a busy guy. He’s an important guy. He’s usually right in the thick of things, but more often than not, when I’ve called his office to check on something in which he is involved, he doesn’t know anything about it. I guess certain things just slip his mind. You know how it is when you’re busy.

Like all my most wonderful dreams, the park [Liberace] was an idea with the built- in nightmare of finding the finances to make it come true. When I first discussed it with my friend Donald Trump, he gave me some great advice. Donald is the young real estate wizard who’s changed the skyline of New York City. When starting a project like this, you have to decide what is most important, make that your top priority, and go from there. He said, “The trouble with you is you think you have to earn this money before you start. It’ll never happen that way. You never use your own money.”

That was news to me, and I wondered what he meant by it. He explained there were people with only one talent, and that was for making money. They had money to burn. They were looking for ways to spend it to make money. To do that, they went after people like a Donald Trump, or a Walt Disney, or, why not, a Liberace—people who were creative enough to envision the fantasies in which they could invest.

Donald was talking about billionaires and not mere millionaires. From his point of view, anybody could make a million. …

According to Donald Trump, I was suddenly a tycoon without even being sure what that meant. … (early 1980s)

from The Wonderful Private World of Liberace, by Liberace (Harper & Row, 1986)

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Lawrence Taylor, football playerImpressive

…Donald Trump, the real estate developer and owner of the New Jersey Generals [of the United States Football League]…wanted to talk to me…

…upstairs to his office. He got right to the point. He wanted me to play for him after my contract with the [New York] Giants was finished. He told me he was building a dynasty that one day would beat any team in the NFL so that when the two leagues finally merged, a certainty, he said, he hoped I would be playing for him. The defense, he promised, would be built around me. This team would be like no other.

It all sounded just perfect—and so I listened, without intending to get into anything with Trump at all. I told him that I appreciated his interest in me but I would need a little time to think.

No problem there.

…to another office where they had a film all lined up waiting to be shown. It was about Donald Trump the man, and what he had done. It was about Trump Tower and the New Jersey Generals, and it was impressive. Everything that was going on was impressive. Donald Trump was impressive: He was young, dynamic, rich, and very articulate; his offices were impressive, his building was impressive, his film was impressive, this show he was putting on for me was impressive. (1983)

from LT: Living on the Edge, by Lawrence Taylor with David Falkner (Times Books, 1987)

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Regis Philbin, talk show hostOn fire

When I came back home to New York in 1983 and was looking for a colorful character to interview for my show, I was told to go get Donald Trump. I took a camera crew over to his Trump Tower, which you couldn’t miss. Not only was it the most spectacular, most blinding, and most beautiful building on Fifth Avenue, but Trump had then most wildly dressed doormen in New York standing at its entrances, too. …

The doorman swung open the portals for me that day, and there he was—thirty-five years old, the hottest young guy in the hottest town. We met in his building’s overwhelming lobby, which features an eighty-five-foot waterfall spilling down over one of the walls. I had never seen anything like it—now this was a lobby! And I was truly just as impressed with him. I wanted to know about this guy—where he came from, how he built this monument to his own dreams, where he was going from here. I thought I’d get a good five minutes out of him. He was on fire. We must have stood there for half an hour, with Trump doing most of the talking, until the camera ran out of tape….

from How I Got This Way, by Regis Philbin (HarperCollins 2011)

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Bob Woolf, lawyer and negotiatorPersonal commercial

…my first meeting with Donald Trump before negotiations began to sign Doug Flutie to a contract to play for Donald’s United States Football League entry, the New Jersey Generals.

…Trump had built quite a reputation for himself. He was flamboyant, aggressive, and unpredictable as well as a fabulously wealthy and successful businessman. I didn’t know which famed Trump to expect: the shrewd developer, the egocentric sportsman, the generous philanthropist, or the would-be politician.

Trump has a private elevator which brings him his guests and business acquaintances, but you have to state your business to the two men who guard it before being escorted to the twenty-sixth floor.

…We were greeted by Trump’s receptionist, who said that Mr. Trump was expecting us. After a few moments Trump himself appeared. We shook hands and he said, “I am running a few minutes late. Please excuse me. Perhaps you would like to step inside and see a short film I have made.”

Trump ushered us into a small, private screening room which seated about twenty. We were the only people there. Trump excused himself and left. The lights went down and the curtains parted and for the next twenty minutes we were shown a slickly produced, visually attractive, highly impressive presentation detailing the triumphs and achievements of Donald Trump. It was impressive. It was his commercial. Maybe he wanted to make sure we knew the extent of his accomplishments. It was his attempt to earn our respect and create the right atmosphere before our negotiations took place. Only after we had seen the film in its entirety were we shown into Mr. Trump’s office. (1984)

from Friendly Persuasion: My Life as a Negotiator, by Bob Woolf (G.P. Putnam’s Sons, 1990)

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Ron Rosenbaum, journalistOver the dealmaker’s desk

…I was too preoccupied assessing Trump’s dream of negotiating a nuclear arms deal with the Soviets to do more than note the curious presence of a golden mirror over Trump’s head.

…I’d never seen a mirrored ceiling over a desktop before.

And the mirrored ceiling over Donald Trump’s desk was no standard-issue blank for that matter. It was composed of golden squares of mirror-finished precious metal alloy. The awe-inspiring effect was to suspend Trump’s desk, his phone set, and Trump himself upside down in a digitalized golden shimmer on the ceiling.

If an age declares its ruling passions in the transactions it chooses to eroticize, then the passions of Manhattan in the eighties are best embodied in the golden mirror over the dealmaker’s desk.

…the Trump wedding [to Melania, in 2005]…Palm Beach…I was the real-life insider, on a great list than included the Clintons, Muhammad Ali…Prince Charles…I had known Donald for years, first encountering him when he bought into the ill-fated US Football League during the 1980s. He was a great outspoken guy with a lot of money. I interviewed him [for the CBS celebrity magazine The Insider] a few times, and when he filed for bankruptcy I called him to commiserate. A few months later I was at one of his casinos in Atlantic City, and his casino manager came over and told me, “You’re on Donald’s short list because you were one of the few people who called him when he was broke and he really valued that.” We had him on my late-night Olympic show, and we would chat from time to time, and he would always take my call. Then he suddenly became DONALD TRUMP and we had a useful relationship: he would use me for publicity and I would use him to show people that I could actually get to him. The relationship was made in ratings heaven…

from I’ll Be Right Back After This: My Memoir, by Pat O’Brien (St. Martin’s Press, 2014)

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Zsa Zsa Gabor, actorHis kind of woman

We [she and husband Frederick von Anhalt] went to New York together and stayed at the Plaza. Ivana and Donald Trump heard we were in town and, although Donald and I had never met, he telephoned me and we ended up chatting for nearly an hour. He was very sweet and told me how he loves European girls, how much he likes my kind of woman, and I could tell he was trying to flirt with me but didn’t quite now how. He was nice and I had the feeling that he was wonderful. Above all, he wanted to know all about Conrad [one of her seven former husbands] and said that he admired him so much and had always wanted to be another Conrad Hilton. (1986)

from One Lifetime Is Not Enough, by Zsa Zsa Gabor with Wendy Leigh (Delacorte, 1991)

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Pete Rose, baseball player and gamblerHit it off

I first met Donald Trump at his Trump Plaza Hotel and Casino in Atlantic City, New Jersey, where I appeared at several autograph shows. He and I hit it off right away because we both went after what we wanted in life and refused to let anyone stand in our way. (1980s)

What can you say about Donald Trump that he hasn’t already said about himself?

I’m going to surprise you—and probably him—with what I’m going to tell you next. Donald’s a very gifted man. In some ways, I believe he is brilliant. I think that his buildings are magnificent additions to the New York City skyline.

But he is also a person of extremes. There’s no in-between with Donald. He’s either your best friend or your worst enemy. Sometimes he’s both—in the same conversation. There are days when his genius sparks him to dizzying heights of creativity. Then there are other, darker days when it causes him to rage at the world for failing to recognize his greatness.

Donald Trump is the Vince Lombardi of developers. For Donald, winning isn’t everything; it is the only thing. What he doesn’t understand is that you can only beat someone who chooses to play your game. I never did. Oh sure, we had the “War at the Shore” [1988 bidding, and attendant trash-talking, for Atlantic City casino-hotels], but in the end he got the Taj Mahal and I got Resorts and Paradise Island. Each of us got what he wanted, which, in my book, is the definition of winning.

Donald has remained in the gaming business and I’m happy to report that he’s doing well with his three Atlantic City properties. He too suffered through the tough economic times, and, like me, he used the bankruptcy mechanisms to reorganize his businesses and get them back on their feet. I love that town, and Donald is an important part of its ongoing success.

from Merv: Making the Good Life Last, by Merv Griffin with David Bender (Simon & Schuster, 2003)

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Garth Drabinsky, movie screen mogul and theatre impresarioDistracted

Donald Trump, our landlord for Cinema III in New York’s Plaza Hotel, was one possible buyer [of Cineplex Odeon]. The day we met in his opulent-but-garish office high up in the Trump Tower in Manhattan, he hardly seemed to hear me as I pitched the sale of our New York circuit. He was completely distracted, and no wonder; his casino, his marriage, and his real-estate empire were only months from crumbling. (1988)

from Closer to the Sun, by Garth Drabinsky with Marq de Villiers (McClelland and Stewart, 1995)

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Eric Idle, comedianLooking good

…The Mandalay Bay sits virtually on the runway of Las Vegas Airport, which is also virtually deserted on this Sunday morning. …

Donald Trump is at breakfast. From where the Donald parks his plane you can practically walk across the street. Although what am I thinking, he probably takes a helicopter here. He looks in good form, the Trump, in excellent shape, with two very healthy-looking young ladies and a business companion. My wife pities the two young women having to be with these older guys, but I don’t agree with her at all. It’s not such a bad job, surely, giving the Donald a Donald. [A Donald English rhyming slang. Donald Duck–well, you work it out.] (early 1990s)

from The Greedy Bastard Diary: A Comic Tour of America by Eric Idle (HarperEntertainment, 2005)

…there wasn’t a week when Trump didn’t phone us [he and Daily News “Hot Copy” co-columnist Linda Stasi] up with a tip or two or didn’t extend an invitation to dinner or a party…

…he can be very engaging, very complimentary, even a little charming. But if you’re smart and you shake out of it, you realize it’s mostly a façade and that everything he says, every second on the phone with you, is just to ensure that the next thing he needs written about himself will make it in the column without a publicist’s push. And that’s the way the relationship goes with him. He works the press like a hooker works the streets. And when you have a gossip column that’s generating major interest and churning out big breaking stories, you put up with Trump’s P.T. Barnum act. But Trump treated us to some of the biggest scoops we ever had and we treated him like a god. It was only after I stepped away from the biz and he stepped in between me and a girlfriend that I had thoughts of pushing him off the roof of one of his gaudy skyscrapers. … (1990)

from Fame: Ain’t It a Bitch, Confessions of a Reformed Gossip Columnist, by A. J. Benza (Talk Miramax Books/Hyperion, 2001)

Donald came up to me in that self-important way of his and gave me a dose of the famous Trump charm. I knew all about his longstanding affair with Marla Maples, but Marla was nowhere to be seen that night—and out of sight, out of Donald’s wandering mind. We started talking about golf. Donald bragged that he had a scratch handicap, but he clearly had other sport in mind.

“You know,” he told me, his eyes searching mine, “I just want to meet a nice, quiet girl who wants to have a family.” He was about as subtle as a sledgehammer: Play my cards right, he was implying, and I might be that lucky girl.

As I laughed to myself about the whole situation, Donald handed me his phone number. That very moment, O. J. arrived and walked up behind me.

“Oh, look honey,” I said, taking the card and passing it on to O. J., “Donald wants you to play golf with him when you get a chance.” (1992)

from The Other Woman: My Years with O. J. Simpson, A Story of Love, Trust, and Betrayal, by Paula Barbieri (Little, Brown, 1997)

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Richard Branson, businessman and adventurerPlotting revenge

…Donald invited me to lunch at his apartment in Manhattan.

I was intrigued. The invitation had come somewhat out of the blue. I turned up to an apartment that was undoubtedly opulent, but not as flashy as I had anticipated. That was not the only part of the lunch that didn’t turn out as expected. Even before the starters had arrived, Donald was warming to what he wanted to talk to me about: the various people he was planning to take revenge on for refusing his request for help.

“I phoned ten people for financial help when I was in trouble,” he said. “Five of those people said they wouldn’t help me.” This rejection had not gone down well: Donald went on to spend the rest of the bizarre lunch telling me how he was going to dedicate his life to destroying those five people.

As I tried to eat my chicken soup, I couldn’t help questioning why on earth he was telling me this. As he continued to run through his list of main offenders in detail, I wondered if he was going to ask me for help. If he had, I would have become the sixth person on his list.

…I left his apartment feeling quite sorry for him.

from Finding my Virginity: The New Autobiography, by Richard Branson (Portfolio/Penguin, 2017)

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Jesse Ventura, Minnesota governor (1999-2002)Knows how to do business

All of a sudden, Donald Trump came forward as a possible alternative [Reform Party presidential candidate]. He thinks a lot like me, and we had several meetings together. I’ve known Trump since the early WrestleManias he staged in Atlantic City, which were the fastest sell-outs he ever had. At least you could look at Trump and say, “This guy knows how to do business.” So I came out in favor of his receiving the Reform Party’s nomination. And Donald has said publicly that, if I ever run for president, he will fully support me, financially and any way that he can. (2000)

from Don’t Start the Revolution Without Me!, by Jesse Ventura with Dick Russell (Skyhorse Publishing, 2008)

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Bill O’Reilly, broadcasterMuch in common

I’ve known Trump for years, and he’s a true force of nature. Unlike presidents or even Oprah Winfrey, Donald doesn’t depend on masses of people [voters or viewers] for his success or power. No, his enormous clout comes from partnering up with a few high rollers who like his maverick style. They want to invest or live in his buildings, gamble in his casinos, and present a powerful image like Trump does.

…I have spent some time with Trump. We are both baseball fans, so a couple of times a year, we’ll go out to Yankee Stadium and, while watching the game, kick world events around. Trump is well informed and insightful. For example, he understands exactly what I’ve done with the [The O’Reilly] Factor [cable television talk show] brand because it is similar to what he’s done with the Trump brand. In addition to having an acute interest in the world, both Trump and I are well known and exceedingly controversial. So we have common ground.

from A Bold Fresh Piece of Humanity, by Bill O’Reilly (Broadway Books, 2008)

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Stormy Daniels, pornographic actressInteresting guy

It was a charity golf tournament in Lake Tahoe. I guess he was there to play golf, and I was there because the company I worked for [Wicked Pictures movie studio] was doing an appearance in the gift room. The first time I met him was actually out on the course. They brought us out to ride around and he kept looking at me and we were introduced. He was introduced to everybody. He kept looking at me and then we ended up riding to another hole in the same golf cart together and he’s like, “I want to come talk to you later,” Later, when he was coming to the gift room, he came to talk to me and asked for my number and I gave it to him. Then he asked me if I wanted to have dinner that night and I was like,” Yeah, of course!” Who would pass up an opportunity to talk to someone so interesting? I wasn’t trying to date him or anything like that. (2006)

Trump’s a polarizing figure, but I love his supreme self-confidence—as confirmed by the titles of his books. Think Like a Billionaire, Think Big and Kick Ass; and my favorite: No Such Thing as Over-Exposure.

Beneath the cocksure bluster, though, Trump’s a very smart businessman…

One of the many fascinating things about Trump is that he’s never touched a drop of alcohol, smoked a cigarette, or tried a drug. He doesn’t even drink coffee.

Dana Cook’s collections of literary, political and show business encounters have appeared in a wide range of newspapers, magazines and journals. His 50th anniversary retrospective on the assassination of Democratic presidential candidate Robert F. Kennedy appeared in CounterpunchJune 1. Contact: cooks.encounters(at)gmail.com